Sodium Hydroxide → 3-Methyl-8-(5-methoxy-2-benzimidazolyl)thio-5,6,7,8-tetrahydroquinoline

HRID 649184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 649184
Cl[C:2]1[NH:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.NC(N)=[S:15].[CH3:17][C:18]1[CH:19]=[N:20][C:21]2[CH:22](Br)[CH2:23][CH2:24][CH2:25][C:26]=2[CH:27]=1.[OH-].[Na+]>O.C(O)C>[CH3:12][O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([S:15][CH:22]3[C:21]4[N:20]=[CH:19][C:18]([CH3:17])=[CH:27][C:26]=4[CH2:25][CH2:24][CH2:23]3)[NH:3][C:4]=2[CH:10]=1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 5191972-Chloro-5-methoxy-1H-benzimidazoleHCID 2723790ThioureaHCID 139602608-Bromo-3-methyl-5,6,7,8-tetrahydroquinoline

Produkt 1

HCID 139602623-Methyl-8-(5-methoxy-2-benzimidazolyl)thio-5,6,7,8-tetrahydroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

0.55 Gram of 2-chloro-5-methoxybenzimidazole, 0.2 g of thiourea and 10 ml of ethanol were mixed together and refluxed for 2 hours. Then, 5 ml of an aqueous solution containing 0.5 g of 3-methyl-8-bromo-5,6,7,8-tetrahydroquinoline and 0.3 g of sodium hydroxide was added thereto, and the resulting mixture was refluxed for 5 hours. After the reaction was completed, ethanol was removed by evaporation, to the residue thus obtained was added water, then extracted with chloroform, the chloroform extract was dried with anhydrous magnesium sulfate, and chloroform was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane/methanol=100/1) to yield 0.5 g of 8-(5-methoxy-2-benzimidazolyl)thio-3-methyl-5,6,7,8-tetrahydroquinoline in the form of colorless caramel-like substance.

Aufarbeitung

  1. temperaturerefluxed for 2 hours
  2. additionwas added
  3. temperaturethe resulting mixture was refluxed for 5 hours
  4. customethanol was removed by evaporation, to the residue
  5. customthus obtained
  6. extractionextracted with chloroform
  7. extractionthe chloroform extract
  8. dry with materialwas dried with anhydrous magnesium sulfate, and chloroform
  9. customwas removed by evaporation
  10. customThe residue thus obtained
  11. customwas purified by means of a silica gel column chromatography (eluent: dichloromethane/methanol=100/1)

Quellen und Nachweise

ORD-Eintrag
ord-69178ee9b4b94831b760d1973e9e75b7
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04738970

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